6-pyridone-2-carbamoyl-azoles and their use as herbicides

ABSTRACT

6-Pyridone-2-carbamoylazoles of the general formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), W, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q represents a 5-membered radical such as oxadiazyl.

The invention relates to the technical field of herbicides, especiallythat of herbicides for the selective control of broad-leaved weeds andweed grasses in crops of useful plants.

WO2012/039141 A1 describes 6-pyridone-2-carbonylcyclohexanediones and6-pyridone-2-carbonylpyrazoles as herbicides. WO 2012/028579 A1discloses N-(tetrazol-5-yl)- and N-(triazol-5-yl)nicotinamides asherbicides. The application EP 11158253, with an earlier priority datebut unpublished at the priority date of the present specification,discloses N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides as herbicides.The application EP 11159115, with an earlier priority date butunpublished at the priority date of the present specification, disclosesN-(1,3,4-oxadiazol-2-yl)nicotinamides as herbicides. However, theseactive compounds are not always sufficiently active against harmfulplants and/or some of them are not sufficiently compatible with someimportant crop plants such as cereal species, corn or rice.

Accordingly, it is an object of the present invention to provide furtherherbicidally active compounds. This object is achieved by the6-pyridone-2-carbamoylazoles according to the invention described below.

The present invention thus provides 6-pyridone-2-carbamoylazoles of theformula (I) or salts thereof

in which

Q represents a radical Q¹, Q², Q³ or Q⁴,

R³ represents (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, wherethese radicals are each substituted by s radicals from the groupconsisting of halogen, cyano, hydroxy, nitro, SiR¹⁰ ₃, PO(OR¹⁰)₂,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, COR^(3a),COOR^(3a), OCOR^(3a), NR^(3a)COR^(3a), NR^(3a)SO₂R^(3b),(C₃-C₆)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the 4last-mentioned radicals are each substituted by p radicals from thegroup consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano andhalogen, and where heterocyclyl carries n oxo groups, or

R³ represents phenyl which is substituted by p radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R^(3a) represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkylor phenyl,

R^(3b) represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁴ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C_(r) C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino,methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl,trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or

heteroaryl, heterocyclyl or phenyl, each of which is substituted by pradicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen,

R⁵ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,CH₂R^(5a), (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR⁶, NHR⁶,methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl,dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl,methylsulfonyl or represents heteroaryl, heterocyclyl, benzyl or phenyl,each of which is substituted by p radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R^(5a) represents acetoxy, acetamido, N-methylacetamido, benzoyloxy,benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,dimethylaminocarbonyl, (C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, or representsheteroaryl or heterocyclyl, each of which is substituted by p radicalsfrom the group consisting of methyl, ethyl, methoxy, trifluoromethyl andhalogen,

X represents (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,OCOOR⁶, OC(O)N(R⁶)₂, OR⁶, OCOR⁶, OSO₂R⁷, (C₁-C₆)-alkyl-S(O)_(n)R⁷,(C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR⁶, (C₁-C₆)-alkyl-OSO₂R⁷,(C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶, (C₁-C₆)-alkyl-CON(R⁶)₂,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR⁶SO₂R⁷, CH₂P(O)(OR¹⁰)₂, (C₁-C₆)-alkyl-aryl,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, where the threelast-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, cyano, nitro, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries n oxo groups,

Z represents hydrogen, halogen, cyano, thiocyanato, nitro,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR⁶, COOR⁶, OR⁶, OCOOR⁶,NR⁶COOR⁶, C(O)N(R⁶)₂, NR⁶C(O)N(R⁶)₂, OC(O)N(R⁶)₂, C(O)NR⁶OR⁶, OSO₂R′,S(O)_(n)R⁷, SO₂OR⁶, SO₂N(R⁶)₂, NR⁶SO₂R⁷, NR⁶COR⁶,(C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R′, (C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶,(C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR¹SO₂R⁷, N(R⁶)₂, P(O)(OR¹⁰)₂, heteroaryl, heterocyclyl orphenyl, where the three last-mentioned radicals are each substituted bys radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,

W represents hydrogen, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,S(O)_(n)R¹⁰,

or

Z and W together with the carbon atoms to which they are attached form afive- or six-membered aromatic ring system in which p carbon atoms arereplaced by heteroatoms from the group consisting of N, O and S, andwhich is substituted by q radicals from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,

-   -   R⁶ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,        (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,        (C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,        (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,        heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycl,        (C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,        (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR⁸-heteroaryl,        (C₁-C₆)-alkyl-NR⁸-heterocyclyl, where the 21 last-mentioned        radicals are substituted by s radicals from the group consisting        of cyano, halogen, nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂,        NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹, NR⁸COR⁸, NR⁸SO2R⁹, CO₂R⁸, COSR⁹,        CON(R⁸)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where        heterocyclyl carries n oxo groups,

R⁷ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO₂R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R⁸ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁹ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl,

R¹⁰ represents (C₁-C₄)-alkyl,

n represents 0, 1 or 2,

p represents 0, 1, 2 or 3,

q represents 0, 1, 2, 3 or 4,

s represents 0, 1, 2, 3, 4 or 5.

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals represent, for example, methyl, ethyl, n- or isopropyl,n-, iso-, tert- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyland 1,3-dimethylbutyl. Analogously, alkenyl represents, for example,allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynylrepresents, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. The multiple bond may be in each case in anyposition of the unsaturated radical. Cycloalkyl represents a carbocyclicsaturated ring system having three to six carbon atoms, for examplecyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Analogously,cycloalkenyl represents a monocyclic alkenyl group having three to sixcarbon ring members, for example cyclopropenyl, cyclobutenyl,cyclopentenyl and cyclohexenyl, where the double bond may be in anyposition.

Halogen represents fluorine, chlorine, bromine or iodine.

Heterocyclyl represents a saturated, semisaturated or fully unsaturatedcyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are fromthe group consisting of oxygen, nitrogen and sulfur, and which mayadditionally be fused by a benzo ring. For example, heterocyclylrepresents piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyland oxetanyl.

Heteroaryl represents an aromatic cyclic radical containing 3 to 6 ringatoms, of which 1 to 4 are from the group consisting of oxygen, nitrogenand sulfur, and which may additionally be fused by a benzo ring. Forexample, heteroaryl represents benzimidazol-2-yl, furanyl, imidazolyl,isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl,pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

When a group is polysubstituted by radicals, this means that this groupis substituted by one or more identical or different radicals from thosementioned.

According to the nature and the bonding of the substituents, thecompounds of the general formula (I) may be present as stereoisomers.If, for example, one or more asymmetric carbon atoms are present, theremay be enantiomers and diastereomers. Stereoisomers likewise occur whenn is 1 (sulfoxides). Stereoisomers can be obtained from the mixturesobtained in the preparation by customary separation methods, for exampleby chromatographic separation processes. It is likewise possible toselectively prepare stereoisomers by using stereoselective reactionswith use of optically active starting materials and/or auxiliaries. Theinvention also relates to all stereoisomers and mixtures thereof whichare encompassed by the general formula (I) but not defined specifically.

The compounds of the formula (I) may form salts. Salts may be formed byaction of a base on compounds of the formula (I). Examples of suitablebases are organic amines such as trialkylamines, morpholine, piperidineand pyridine, and the hydroxides, carbonates and hydrogencarbonates ofammonium, alkali metals or alkaline earth metals, in particular sodiumhydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,sodium hydrogencarbonate and potassium hydrogencarbonate.

These salts are compounds in which the acidic hydrogen is replaced by anagriculturally suitable cation, for example metal salts, in particularalkali metal salts or alkaline earth metal salts, in particular sodiumand potassium salts, or else ammonium salts, salts with organic aminesor quaternary ammonium salts, for example with cations of the formula[NR^(a)R^(b)R^(c)R^(d)]⁺, in which R^(a) to R^(d) in each caseindependently of one another are an organic radical, in particularalkyl, aryl, aralkyl or alkylaryl. Also useful are alkylsulfonium andalkylsulfoxonium salts, such as (C₁-C₄)-trialkylsulfonium and(C₁-C₄)-trialkylsulfoxonium salts.

Preference is given to compounds of the general formula (I) in which

Q represents a radical Q¹, Q², Q³ or Q⁴,

R³ represents (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, wherethese radicals are each substituted by s radicals from the groupconsisting of halogen, cyano, nitro, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl or phenyl, where the 4 last-mentioned radicals are eachsubstituted by p radicals from the group consisting of methyl, ethyl,methoxy, trifluoromethyl, cyano and halogen, and where heterocyclylcarries n oxo groups, or

R³ represents phenyl which is in each case substituted by p radicalsfrom the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R⁴ represents (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, (C₁-C₄)-alkylcarbonylamino,benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy,methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen,amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,methoxymethyl, 1,2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophenyl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl,benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or representsphenyl which is in each case substituted by p radicals from the groupconsisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,

R⁵ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl, benzyl,pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine,dimethylamino, or represents phenyl which is substituted by p radicalsfrom the group consisting of methyl, methoxy, trifluoromethyl andhalogen,

X represents (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,OCOOR⁶, OC(O)N(R⁶)₂, OR⁶, OCOR⁶, OSO₂R⁷, (C₁-C₆)-alkyl-S(O)_(n)R⁷,(C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR⁶, (C₁-C₆)-alkyl-OSO₂R⁷,(C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶, (C₁-C₆)-alkyl-CON(R⁶)₂,(C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶, (C₁-C₆)-alkyl-NR⁶SO₂R⁷,CH₂P(O)(OR¹⁰)₂, (C₁-C₆)-alkyl-aryl, (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkyl-heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of halogen,cyano, nitro, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries noxo groups,

Z represents hydrogen, halogen, cyano, thiocyanato, nitro,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR⁶, COOR⁶, OCOOR⁶, NR⁶COOR⁶, C(O)N(R⁶)₂, NR⁶C(O)N(R⁶)₂, OC(O)N(R⁶)₂,C(O)NR⁶OR⁶, OSO₂R⁷, S(O)_(n)R⁷, SO₂OR⁶, SO₂N(R⁶)₂, NR⁶SO₂R⁷, NR⁶COR⁶,(C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R′, (C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶,(C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR¹SO₂R⁷, N(R⁶)₂, P(O)(OR¹⁰)₂, heteroaryl, heterocyclyl orphenyl, where the last three radicals are in each case substituted by sradicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,

W represents hydrogen, halogen, methyl, trifluoromethyl, S(O)_(n)Me,

or

Z and W together with the carbon atoms to which they are attached form afive- or six-membered aromatic ring system in which p carbon atoms arereplaced by heteroatoms from the group consisting of N, O and S, andwhich is substituted by q radicals from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy,

R⁶ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycl,(C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR⁸-heteroaryl,(C₁-C₆)-alkyl-NR⁸-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO2R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R⁷ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO₂R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R⁸ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁹ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl,

R¹⁰ represents (C₁-C₄)-alkyl,

n represents 0, 1 or 2,

p represents 0, 1, 2 or 3,

q represents 0, 1, 2, 3 or 4,

s represents 0, 1, 2, 3, 4 or 5.

Particular preference is given to compounds of the general formula (I)in which

Q represents a radical Q¹, Q², Q³ or Q⁴,

R³ represents (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or (C₂-C₈)-alkynyl, each ofwhich is substituted by s radicals from the group consisting of halogen,cyano, nitro, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy,

R⁴ represents (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, (C₁-C₄)-alkylcarbonylamino,benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy,methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen,amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,methoxymethyl, 1,2,4-triazol-1H, 1-pyrazol-1H, 2-thiophenyl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl,benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or representsphenyl which is in each case substituted by s radicals from the groupconsisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,

R⁵ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl, benzyl,pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine,dimethylamino, or represents phenyl which is substituted by p radicalsfrom the group consisting of methyl, methoxy, trifluoromethyl andhalogen;

X represents (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, OR⁶,S(O)_(n)R⁷, (C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶,(C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR⁶SO₂R⁷, (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkylheterocyclyl, where the two last-mentioned radicals are ineach case substituted by s radicals from the group consisting ofhalogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries noxo groups,

Z represents hydrogen, halogen, cyano, thiocyanato, nitro,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR⁶, COOR⁶, OCOOR⁶, NR⁶COOR⁶, C(O)N(R⁶)₂, NR⁶C(O)N(R⁶)₂, OC(O)N(R⁶)₂,C(O)NR⁶OR⁶, OSO₂R⁷, S(O)_(n)R⁷, SO₂OR⁶, SO₂N(R⁶)₂, NR⁶SO₂R⁷, NR⁶COR⁶,(C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R⁷, (C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶,(C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR¹SO₂R⁷, N(R⁶)₂, P(O)(OR¹⁰)₂, heteroaryl, heterocyclyl orphenyl, where the 3 last-mentioned radicals are in each case substitutedby s radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,

W represents hydrogen, chlorine, methyl or trifluoromethyl,

or

Z and W together with the carbon atoms to which they are attached form afive- or six-membered aromatic ring system in which p carbon atoms arereplaced by heteroatoms from the group consisting of N, O and S, andwhich is substituted by q radicals from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₄)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-methyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy,

R⁶ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycl,(C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR⁸-heteroaryl,(C₁-C₆)-alkyl-NR⁸-heterocyclyl, where the 21 last-mentioned radicals arein each case substituted by s radicals from the group consisting ofcyano, halogen, nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸,COR⁸, OCOR⁸, SCOR⁹, NR⁸COR⁸, NR⁸SO2R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R⁷ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals areeach substituted by s radicals from the group consisting of cyano,halogen, nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸,OCOR⁸, SCOR⁹, NR⁸COR⁸, NR⁸SO₂R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R⁸ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁹ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl,

R¹⁰ represents (C₁-C₄)-alkyl,

n represents 0, 1 or 2,

p represents 0, 1, 2 or 3,

q represents 0, 1, 2, 3 or 4,

s represents 0, 1, 2, 3, 4 or 5.

In all the formulae specified hereinafter, the substituents and symbolshave the same meaning as described in formula (I), unless defineddifferently.

Compounds according to the invention where Q=Q¹ or Q² can be prepared,for example, by the method indicated in WO2012/039141 A1. Compoundsaccording to the invention where Q=Q³ can be prepared, for example, bythe method indicated in EP 11158253. Compounds according to theinvention where Q=Q⁴ can be prepared, for example, by the methodindicated in EP 11159115.

The 6-pyridone-2-carbonyl chlorides (II) and the 6-pyridone-2-carboxylicacids (III) on which they are based can be prepared, for example,according to Scheme 1:

The 6-pyridone-2-carboxylic esters (IV) can be prepared, for example,according to Scheme 2 from the NH-6-pyridone-2-carboxylic esters (V).

The 6-pyridone-2-carboxylic esters (IV) can also be prepared, forexample, according to Scheme 3 from the5-hydroxy-6-pyridone-2-carboxylic esters (VI). To this end, initiallythe hydroxyl group is converted into a sulfonate group, and this is thenremoved hydrogenolytically with the aid of a catalyst.

Compounds (VIII) where X═OR⁶ can be prepared, for example, according toScheme 4 by oxidation of the ester (V) to the N-hydroxy compound (VII)according to the method described in J. Med. Chem (2002), 45(18),3963-3971, followed by the introduction of the R⁶ group.

NH-pyrid-6-one-2-carboxylic esters (V) can be prepared, for example,analogously to the methods described in WO 2005/058037 A1.

It may be expedient to change the order of reaction steps. Thus, benzoicacids carrying a sulfoxide cannot be converted directly into their acidchlorides. Here, it is advisable to prepare initially, at the thioetherstage, the amide and then to oxidize the thioether to the sulfoxide.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the abovementioned reactions can also be preparedin a parallelized manner, in which case this may be accomplished in amanual, partly automated or fully automated manner. It is possible, forexample, to automate the conduct of the reaction, the work-up or thepurification of the products and/or intermediates. Overall, this isunderstood to mean a procedure as described, for example, by D. Tiebesin Combinatorial Chemistry—Synthesis, Analysis, Screening (editor:Günther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MultiPROBE Automated Workstationsfrom PerkinElmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the general formula (I) and salts thereofor of intermediates which occur in the course of preparation, availableapparatuses include chromatography apparatuses, for example from ISCO,Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be purchased, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, the compounds of the generalformula (I) and salts thereof can be prepared completely or partially bysolid-phase supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis,Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocols,which are known from the literature and which for their part may beperformed manually or in an automated manner, to be carried out. Thereactions can be performed, for example, by means of IRORI technology inmicroreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif.92064, USA.

Both in the solid and in the liquid phase, individual or severalsynthesis steps may be supported by the use of microwave technology. Thespecialist literature describes a series of experimental protocols, forexample in Microwaves in Organic and Medicinal Chemistry (editor: C. O.Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described here gives compounds of theformula (I) and salts thereof in the form of substance collections,which are called libraries. The present invention also provideslibraries comprising at least two compounds of the formula (I) and saltsthereof.

The compounds of the formula (I) according to the invention (and/orsalts thereof), collectively referred to hereinafter as “compoundsaccording to the invention”, have excellent herbicidal efficacy againsta broad spectrum of economically important monocotyledonous anddicotyledonous annual weed plants. The active compounds also have goodcontrol over perennial harmful plants which are difficult to control andproduce shoots from rhizomes, root stocks or other perennial organs.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more compound(s) according to the inventionis/are applied to the plants (for example weed plants such asmonocotyledonous or dicotyledonous weeds or unwanted crop plants), tothe seeds (for example grains, seeds or vegetative propagules such astubers or shoot parts with buds) or to the area on which the plants grow(for example the area under cultivation). The compounds according to theinvention can be deployed, for example, prior to sowing (if appropriatealso by incorporation into the soil), prior to emergence or afteremergence. Specific examples of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the compounds according to the invention are as follows, though theenumeration is not intended to impose a restriction to particularspecies:

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

When the compounds according to the invention are applied to the soilsurface before germination, either the weed seedlings are preventedcompletely from emerging or the weeds grow until they have reached thecotyledon stage, but then stop growing and eventually, after three tofour weeks have elapsed, die.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth stops after the treatment, and the harmful plantsremain at the growth stage at the time of application, or they diecompletely after a certain time, so that in this manner competition bythe weeds, which is harmful to the crop plants, is eliminated very earlyand in a lasting manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, ormonocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, are damaged only to aninsignificant extent, or not at all, depending on the structure of therespective compound according to the invention and its application rate.For these reasons, the present compounds are very suitable for theselective control of unwanted plant growth in plant crops such asagriculturally useful plants or ornamentals.

In addition, the compounds according to the invention (depending ontheir particular structure and the application rate deployed) haveoutstanding growth-regulating properties in crop plants. They interveneto regulate the plant's metabolism and can thus be used for controlledinfluence on plant constituents and to facilitate harvesting, forexample by triggering desiccation and stunted growth. In addition, theyare also suitable for general control and inhibition of unwantedvegetative growth without killing the plants. Inhibiting vegetativegrowth plays a major role for many monocotyledonous and dicotyledonouscrops, since, for example, this can reduce or completely preventlodging.

By virtue of their herbicidal and plant-growth-regulating properties,the active compounds can also be used for controlling harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, transgenic plants are notable for specialadvantageous properties, for example for resistances to certainpesticides, in particular certain herbicides, resistances to plantdiseases or organisms that cause plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or with a different fatty acidcomposition in the harvested material.

It is preferred, with respect to transgenic crops, to use the compoundsaccording to the invention in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet/sorghum, rice and corn or else crops of sugarbeet, cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. It is preferred to employ the compounds according to theinvention as herbicides in crops of useful plants which are resistant,or have been made resistant by recombinant means, to the phytotoxiceffects of the herbicides.

Preference is given to the use of the compounds according to theinvention or salts thereof in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet/sorghum, rice, cassava and corn, or else cropsof sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas andother vegetables. Preferably, the compounds according to the inventioncan be used as herbicides in crops of useful plants which are resistant,or have been made resistant by recombinant means, to the phytotoxiceffects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to plants which have occurred to date consist,for example, in traditional breeding methods and the generation ofmutants. Alternatively, novel plants with modified properties can begenerated with the aid of recombinant methods (see, for example,EP-A-0221044, EP-A-0131624). For example, there have been manydescriptions of:

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (for example WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        of the sulfonylurea type (EP-A-0257993, U.S. Pat. No.        5,013,659),    -   transgenic crop plants, for example cotton, with the ability to        produce Bacillus thuringiensis toxins (Bt toxins) which make the        plants resistant to particular pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are distinguished by higher yields        or better quality,    -   transgenic crop plants which are distinguished by a combination,        for example of the abovementioned novel properties (“gene        stacking”)

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg, or Christou, “Trends in Plant Science” 1(1996) 423-431.

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or a sequence change by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. For the joining of theDNA fragments to one another, adaptors or linkers can be attached to thefragments; see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y.; or Winnacker “Gene and Klone” [Genes and Clones],VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis possible to use DNA molecules which encompass the entire codingsequence of a gene product inclusive of any flanking sequences which maybe present, and also DNA molecules which only encompass portions of thecoding sequence, it being necessary for these portions to be long enoughto have an antisense effect in the cells. The use of DNA sequences whichhave a high degree of homology to the coding sequences of a geneproduct, but are not completely identical to them, is also possible.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, in order to achieve localization in a particularcompartment, it is possible, for example, to join the coding region toDNA sequences which ensure localization in a particular compartment.Such sequences are known to those skilled in the art (see, for example,Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl.Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991),95-106). The nucleic acid molecules can also be expressed in theorganelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive whole plants. In principle, the transgenic plants may be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

For instance, it is possible to obtain transgenic plants whoseproperties are altered by overexpression, suppression or inhibition ofhomologous (=natural) genes or gene sequences, or expression ofheterologous (=foreign) genes or gene sequences.

Preferably, the compounds according to the invention can be used intransgenic crops which are resistant to growth regulators, for exampledicamba, or to herbicides which inhibit essential plant enzymes, forexample acetolactate synthases (ALS), EPSP synthases, glutaminesynthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or toherbicides from the group of the sulfonylureas, the glyphosates,glufosinates or benzoylisoxazoles and analogous active compounds.

On employment of the active compounds according to the invention intransgenic crops, not only do the effects toward weed plants observed inother crops occur, but often also effects which are specific toapplication in the particular transgenic crop, for example an altered orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants. The invention therefore also provides for the use of thecompounds according to the invention as herbicides for control of weedplants in transgenic crop plants.

The compounds according to the invention can be applied in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant growth-regulatingcompositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in variousways, according to the biological and/or physicochemical parametersrequired. Examples of possible formulations include: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), seed-dressing products,granules for broadcasting and soil application, granules (GR) in theform of microgranules, sprayable granules, coated granules andadsorption granules, water-dispersible granules (WG), water-solublegranules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd.London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], volume 7, C. HanserVerlag Munich, 4th ed. 1986.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active ingredient, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. Toprepare the wettable powders, the herbicidally active compounds areground finely, for example in customary apparatus such as hammer mills,blower mills and air-jet mills, and simultaneously or subsequently mixedwith the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). Emulsifiersused may, for example, be: calcium alkylarylsulfonates such as calciumdodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acidpolyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycolethers, propylene oxide-ethylene oxide condensation products, alkylpolyethers, sorbitan esters, for example sorbitan fatty acid esters, orpolyoxyethylene sorbitan esters, for example polyoxyethylene sorbitanfatty acid esters.

Dusts are obtained by grinding the active compound with finelydistributed solid substances, for example talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of commercial bead millswith optional addition of surfactants as already listed above, forexample, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be prepared either by spraying the active substance ontoadsorptive granular inert material or by applying active substanceconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylates or mineral oils. Suitable active compoundscan also be granulated in the manner customary for the production offertilizer granules—if desired as a mixture with fertilizers.

Water-dispersible granules are prepared generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York1973, pp. 8-57.

For further details regarding the formulation of crop protection agents,see, for example, G. C. Klingman, “Weed Control as a Science”, JohnWiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S.A. Evans, “Weed Control Handbook”, 5th ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of compounds according to theinvention.

In wettable powders, the active compound concentration is, for example,about 10 to 90% by weight, the remainder to 100% by weight consisting ofcustomary formulation constituents. In emulsifiable concentrates, theactive ingredient concentration may be about 1 to 90% and preferably 5to 80% by weight. Formulations in the form of dusts comprise 1 to 30% byweight of active compound, preferably usually 5 to 20% by weight ofactive compound; sprayable solutions contain about 0.05 to 80,preferably 2 to 50, % by weight of active compound. In the case ofwater-dispersible granules, the active compound content depends partlyon whether the active compound is present in liquid or solid form and onwhich granulation assistants, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary tackifiers, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Preparations in the form ofdusts, granules for soil application or granules for sowing andsprayable solutions are usually not diluted further with other inertsubstances prior to application.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including temperature, humidity and thetype of herbicide used. It can vary within wide limits, for examplebetween 0.001 and 1.0 kg/ha or more active substance, but it ispreferably between 0.005 and 750 g/ha.

The examples below illustrate the invention.

A. CHEMICAL EXAMPLES 1. Synthesis of5-chloro-1-methyl-N-(1-methyltetrazol-5-yl)pyrid-6-one-2-carboxamide,(Table Example No. 1-31)

At 0° C., 9.45 g (75 mmol) of dimethyl sulfate are added to 11.24 g (60mmol) of methyl 5-chloropyrid-6-one-2-carboxylate and 10.36 g (75 mmol)of potassium carbonate in 60 ml of DMF. The mixture is allowed to warmto room temperature (RT), and after 16 h water and ethyl acetate areadded. The organic phase is washed repeatedly with water, then with sat.sodium bicarbonate solution and with brine. After drying andconcentration, the residue is purified by column chromatography usingheptane/ethyl acetate.

Fraction A 3.88 g (yield 32%) of methyl5-chloro-6-methoxypyridine-2-carboxylate Fraction B 5.18 g (yield 43%)of methyl 5-chloro-1-methylpyrid-6-one-2-carboxylate At 0° C., 584 mg(7.5 mmol) of sodium thiomethoxide are added to 604 mg (3 mmol) ofmethyl 5-chloro-1-methylpyrid-6-one-2-carboxylate in 6 ml of DMF. Themixture is allowed to warm to RT, and after 3 h 2N HCl and ethyl acetateare added. The organic phase is washed repeatedly with water, then withbrine. Drying and concentration gives5-methylsulfenyl-1-methylpyrid-6-one-2-carboxylic acid. Yield 236 mg(40%). At 0° C., 173 mg (1.45 mmol) of thionyl chloride are added to 231mg (1.16 mmol) of 5-methylsulfenyl-1-methylpyrid-6-one-2-carboxylic acidand 176 mg (1.74 mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine.The mixture is stirred at RT for 16 h. The reaction is then quenchedwith a little water, the pyridine is evaporated and the residue ispurified by HPLC. Yield 74 mg (23%).

2. Synthesis ofN-(1-methyltetrazol-5-yl)-1-methoxy-5-trifluoromethylpyrid-6-one-2-carboxamide,(Table Example No. 1-25)

A mixture of 0.8 ml of H₂O₂ (30% strength) in 3 ml of acetic acid isadded to 1.4 g (6 mmol) of methyl5-trifluoromethylpyrid-6-one-2-carboxylate in 5 ml of trifluoroaceticacid and 4 ml of acetic acid, and the mixture is heated at 80° C. for 12h. The mixture is then diluted with ethyl acetate, and washed with 2Nsodium bisulfite solution and repeatedly with brine. Drying andconcentration gives methyl1-hydroxy-5-trifluoromethylpyrid-6-one-2-carboxylate which is reactedfurther without purification. At 0° C., 1.89 g (15 mmol) of dimethylsulfate are added to the residue and 2.1 g (15 mmol) of potassiumcarbonate in 10 ml of DMF. The mixture is allowed to warm to RT, andafter 2 h water, 2N HCl and ethyl acetate are added. The organic phaseis washed repeatedly with water, then with sat. sodium bicarbonatesolution and with brine. After drying and concentration, the methyl1-methoxy-5-trifluoromethylpyrid-6-one-2-carboxylate is reacted furtherwithout purification. At 0° C., 5 ml of 2N NaOH are added to the residuein 5 ml of methanol, and after 30 min the mixture is acidified with 2NHCl. The mixture is diluted with ethyl acetate, the phases are separatedand the organic phase is washed repeatedly with brine. Drying andconcentration gives 1-methoxy-5-trifluoromethylpyrid-6-one-2-carboxylicacid. Yield 830 mg (58%). At 0° C., 149 mg (1.25 mmol) of thionylchloride are added to 237 mg (1.0 mmol) of1-methoxy-5-trifluoromethylpyrid-6-one-2-carboxylic acid and 147 mg (1.5mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine. The mixture isstirred at RT for 16 h. 2N HCl and ethyl acetate are then added, thephases are separated and the organic phase is washed repeatedly withbrine. After drying and concentration, the residue is purified by HPLC.Yield 122 mg (38%).

3. Synthesis of1-benzyl-5-trifluoromethyl-N-(1-methyltetrazol-5-yl)pyrid-6-one-2-carboxamide,(Table Example No. 1-15)

At 0° C., 1.3 ml (11 mmol) of benzyl bromide are added to 2.21 g (10mmol) of methyl 5-trifluoromethylpyrid-6-one-2-carboxylate and 2.07 g(15 mmol) of potassium carbonate in 10 ml of DMF. The mixture is allowedto warm to RT, and after 5 h water and ethyl acetate are added. Theorganic phase is washed repeatedly with water, then with saturatedNaHCO₃ solution and with brine. After drying and concentration, theresidue is purified by column chromatography using heptane/ethylacetate.

Fraction A 1.55 g (yield 50%) of methyl6-benzyloxy-5-trifluoromethylpyridine-2-carboxylate

Fraction B 1.19 g (yield 38%) of methyl1-benzyl-5-trifluoromethylpyrid-6-one-2-carboxylate

4 ml of 2N aqueous sodium hydroxide solution are added to 1.19 g (3.9mmol) of methyl 1-benzyl-5-trifluoromethylpyrid-6-one-2-carboxylate in 8ml of MeOH, and after 30 min the mixture is acidified with 2N HCl. Themixture is diluted with ethyl acetate and, after phase separation,washed repeatedly with brine. Drying and concentration gives1-benzyl-5-trifluoromethylpyrid-6-one-2-carboxylic acid.

At 0° C., 155 mg (1.3 mmol) of thionyl chloride are added to 297 mg (1mmol) of 1-benzyl-5-trifluoromethylpyrid-6-one-2-carboxylic acid and 149mg (1.5 mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine. Themixture is stirred at RT for 16 h. 2N HCl and ethyl acetate are thenadded, the phases are separated and the organic phase is washedrepeatedly with brine. After drying and concentration, the residue ispurified by HPLC. Yield 277 mg (73%).

4. Synthesis of7-methyl-N-(1-methyltetrazol-5-yl)-1,7-naphthyridin-8(7H)-one-6-carboxamide,(Table Example No. 5-3)

At room temperature, 375 mg (1.05 mmol) ofN-phenylbis(trifluoromethanesulfonimide) are added to 234 mg (1 mmol) ofmethyl 5-hydroxy-7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylate (J.Heterocyclic Chem. (1999), 36, 979-984) and 111 mg (1.1 mmol) oftriethylamine in 3 ml of DCM. After 1 h, the mixture is quenched withsaturated NaHCO₃ solution. The organic phase is separated off, dried andconcentrated. The residue is dissolved in 8 ml of ethanol, 164 mg (2mmol) of sodium acetate and 10 mg of Pd/C (10%) are added and themixture is stirred under an atmosphere of hydrogen for 8 h. The catalystis then filtered off and the solution is concentrated and taken up insat. NaHCO₃ solution and DCM. The org. phase is separated off, dried andconcentrated and the residue is purified by column chromatography usingheptane/ethyl acetate. Yield 100 mg (46%) of methyl7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylate.

100 mg of methyl 7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylate in 2ml of methanol and 1 ml of 2N aqueous sodium hydroxide solution arestirred for 3 h, the mixture is acidified with 2N hydrochloric acid andthe crystals obtained are filtered off with suction. Yield 60 mg (64%)of 7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylic acid.

At 0° C., 114 mg (0.96 mmol) of thionyl chloride are added to 150 mg(0.74 mmol) of 7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylic acid and110 mg (1.1 mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine. Themixture is stirred at RT for 16 h. The reaction is then quenched with alittle water, the pyridine is evaporated and the residue is purified byHPLC. Yield 27 mg (13%).

The examples listed in the tables below were prepared analogously to themethods mentioned above or can be obtained analogously to the methodsmentioned above. These compounds are very particularly preferred.

The abbreviations used mean:

Et=ethyl Me=methyl nPr=n-propyl cPr=cyclopropyl Bn=benzyl Ph=phenyl

TABLE 1 Compounds of the general formula (I) according to the invention,in which Q represents Q¹

Physical data No. R³ X Z (¹H-NMR, DMSO-d₆, 400 MHz) 1-1 Me Me H 12.05(brs, 1H), 7.53 (dd, 1H), 6.72 (brd, 1H), 6.63 (dd, 1H), 3.98 (s, 3H),3.47 (s, 3H) 1-2 Me Me Me 11.93 (brs, 1H), 7.43 (dd, 1H), 6.79 (d, 1H),3.98 (s, 3H), 3.49 (s, 3H), 2.08 (d, 3H) 1-3 Me Me CF₃ 8.15 (d, 1H),6.69 (d, 1H), 3.99 (s, 3H), 3.82 (s, 3H) 1-4 Et Me CF₃ 7.90 (d, 1H),6.41 (d, 1H), 4.14 (q, 2H), 3.53 (s, 3H), 1.35 (t, 3H) 1-5 nPr Me CF₃7.87 (d, 1H), 6.33 (d, 1H), 4.04 (m, 2H), 3.53 (s, 3H), 1.76 (m, 2H),0.84 (t, 3H) 1-6 C₂H₄OCH₃ Me CF₃ 7.87 (d, 1H), 6.33 (d, 1H), 4.46 (t,2H), 3.68 (t, 2H), 3.52 (s, 3H), 3.21 (s, 3H) 1-7 Me Et CF₃ 12.3 (brs,1H), 8.11 (d, 1H), 6.83 (d, 1H), 4.05 (q, 2H), 4.01 (s, 3H), 1.28 (t,3H) 1-8 Et Et CF₃ 1-9 nPr Et CF₃ 1-10 C₂H₄OCH₃ Et CF₃ 1-11 Me CH₂cPr CF₃12.35 (brs, 1H), 8.12 (d, 1H), 6.88 (d, 1H), 4.01 (d, 2H), 4.00 (s, 3H),1.22 (m, 1H), 0.48 (m, 2H), 0.38 (m, 2H) 1-12 Et CH₂cPr CF₃ 1-13 nPrCH₂cPr CF₃ 1-14 C₂H₄OCH₃ CH₂cPr CF₃ 1-15 Me Bn CF₃ 7.94 (d, 1H),7.28-7.21 (m, 5H), 6.53 (d, 1H), 5.55 (s, 2H), 3.52 (s, 3H) 1-16 Et BnCF₃ 1-17 nPr Bn CF₃ 1-18 C₂H₄OCH₃ Bn CF₃ 1-19 Me C₂H₄OCH₃ CF₃ 12.2 (brs,1H), 8.12 (d, 1H), 6.88 (d, 1H), 4.43 (t, 2H), 3.99 (s, 3H), 3.52 (t,2H), 3.22 (s, 3H) 1-20 Et C₂H₄OCH₃ CF₃ 1-21 nPr C₂H₄OCH₃ CF₃ 1-22C₂H₄OCH₃ C₂H₄OCH₃ CF₃ 1-23 Me allyl CF₃ 12.25 (brs, 1H), 8.17 (d, 1H),6.89 (d, 1H), 5.91 (ddt, 1H), 5.22 (d, 1H), 5.07 (d, 1H), 4.77 (d, 2H),3.98 (s, 3H), 3.42 (t, 1H) 1-24 Me propargyl CF₃ 8.17 (d, 1H), 6.98 (d,1H), 4.99 (d, 2H), 4.01 (s, 3H), 3.42 (t, 1H) 1-25 Me OMe CF₃ 12.3 (brs,1H), 8.13 (d, 1H), 6.84 (d, 1H), 4.09 (s, 3H), 4.00 (s, 3H) 1-26 Et OMeCF₃ 1-27 nPr OMe CF₃ 1-28 C₂H₄OCH₃ OMe CF₃ 1-29 Me Me Ph 12.06 (brs,1H), 7.75-7.7 (m, 3H), 7.43-7.36 (m, 3H), 6.85 (d, 1H), 4.01 (s, 3H),3.56 (s, 3H) 1-30 Me Me OMe 1-31 Me Me Cl 12.1 (brs, 1H), 7.91 (d, 1H),6.78 (d, 1H), 3.99 (s, 3H), 3.56 (s, 3H) 1-32 Et Me Cl 1-33 nPr Me Cl1-34 C₂H₄OCH₃ Me Cl 1-35 Me Bn Cl 1-36 Et Bn Cl 1-37 nPr Bn Cl 1-38C₂H₄OCH₃ Bn Cl 1-39 Me OMe Cl 12.2 (brs, 1H), 7.94 (d, 1H), 6.75 (d,1H), 4.08 (s, 3H), 3.98 (s, 3H) 1-40 Et OMe Cl 1-41 nPr OMe Cl 1-42C₂H₄OCH₃ OMe Cl 1-43 Me Et Cl 1-44 Et Et Cl 1-45 nPr Et Cl 1-46 C₂H₄OCH₃Et Cl 1-47 Me CH₂cPr Cl 1-48 Et CH₂cPr Cl 1-49 nPr CH₂cPr Cl 1-50C₂H₄OCH₃ CH₂cPr Cl 1-51 Me C₂H₄OCH₃ Cl 1-52 Et C₂H₄OCH₃ Cl 1-53 nPrC₂H₄OCH₃ Cl 1-54 C₂H₄OCH₃ C₂H₄OCH₃ Cl 1-55 Me Me Br 12.1 (brs, 1H), 8.09(d, 1H), 6.69 (d, 1H), 3.99 (s, 3H), 3.55 (s, 3H) 1-56 Me Me SMe 11.92(brs, 1H), 7.22 (d, 1H), 6.87 (d, 1H), 3.97 (s, 3H), 3.54 (s, 3H), 2.38(s, 3H) 1-57 Et Me SMe 1-58 nPr Me SMe 1-59 C₂H₄OCH₃ Me SMe 1-60 Me BnSMe 1-61 Et Bn SMe 1-62 nPr Bn SMe 1-63 C₂H₄OCH₃ Bn SMe 1-64 Me OMe SMe1-65 Et OMe SMe 1-66 nPr OMe SMe 1-67 C₂H₄OCH₃ OMe SMe 1-68 Me Me SEt11.90 (brs, 1H), 7.30 (d, 1H), 6.84 (d, 1H), 3.97 (s, 3H), 3.53 (s, 3H),2.91 (q, 2H), 1.29 (t, 3H) 1-69 Et Me SEt 1-70 nPr Me SEt 1-71 C₂H₄OCH₃Me SEt 1-72 Me Bn SEt 1-73 Et Bn SEt 1-74 nPr Bn SEt 1-75 C₂H₄OCH₃ BnSEt 1-76 Me OMe SEt 1-77 Et OMe SEt 1-78 nPr OMe SEt 1-79 C₂H₄OCH₃ OMeSEt 1-80 Me Me SO₂Me 12.28 (brs, 1H), 8.23 (d, 1H), 6.91 (d, 1H), 4.01(s, 3H), 3.57 (s, 3H), 3.31 (s, 3H) 1-81 Et Me SO₂Me 1-82 nPr Me SO₂Me1-83 C₂H₄OCH₃ Me SO₂Me 1-84 Me Bn SO₂Me 1-85 Et Bn SO₂Me 1-86 nPr BnSO₂Me 1-87 C₂H₄OCH₃ Bn SO₂Me 1-88 Me OMe SO₂Me 1-89 Et OMe SO₂Me 1-90nPr OMe SO₂Me 1-91 C₂H₄OCH₃ OMe SO₂Me 1-92 Me Me SO₂Et 12.25 (brs, 1H),8.23 (d, 1H), 6.91 (d, 1H), 4.00 (s, 3H), 3.56 (s, 3H), 3.49 (q, 2H),1.13 (t, 3H) 1-93 Et Me SO₂Et 1-94 nPr Me SO₂Et 1-95 C₂H₄OCH₃ Me SO₂Et1-96 Me Bn SO₂Et 1-97 Et Bn SO₂Et 1-98 nPr Bn SO₂Et 1-99 C₂H₄OCH₃ BnSO₂Et 1-100 Me OMe SO₂Et 1-101 Et OMe SO₂Et 1-102 nPr OMe SO₂Et 1-103C₂H₄OCH₃ OMe SO₂Et 1-104 Me CH₂(3,4- CF₃ 12.20 (brs, 1H), 8.18 (d, 1H),6.92 (d, 1H), 6.85 methylenedioxyphenyl) (d, 1H), 6.76 (d, 1H), 6.67(dd, 1H), 5.99 (s, 2H), 5.28 (s, 2H), 3.90 (s, 3H) 1-105 Et CH₂(3,4- CF₃12.10 (brs, 1H), 8.17 (d, 1H), 6.91 (d, 1H), 6.86 methylenedioxyphenyl)(d, 1H), 6.76 (d, 1H), 6.66 (dd, 1H), 6.00 (s, 2H), 5.30 (s, 2H), 4.18(q, 2H), 1.38 (t, 3H) 1-106 Me CH₂(3- CF₃ 12.30 (brs, 1H), 8.21 (d, 1H),6.99 (d, 1H), 6.24 methylisoxazol-5-yl) (s, 1H), 5.47 (s, 2H), 3.96 (s,3H), 2.19 (s, 3H) 1-107 Me CH₂(3,5- CF₃ 12.37 (brs, 1H), 8.19 (d, 1H),6.97 (d, 1H), 6.39 dimethylpyrazol-1- (s, 2H), 5.81 (1, 2H), 4.07 (s,3H), 2.38 (s, 3H), yl) 2.06 (s, 3H) 1-108 Me CH₂(thiophen-2-yl) CF₃12.27 (brs, 1H), 8.16 (d, 1H), 7.48 (dd, 1H), 7.04 (dd, 1H), 6.97 (dd,1H), 6.92 (d, 1H), 5.53 (s, 2H), 3.96 (s, 3H) 1-109 Me Me 3,5-F₂—Ph12.12 (brs, 1H), 7.93 (d, 1H), 7.56 (ddd, 2H), 7.26 (dt, 1H), 6.87 (d,1H), 4.01 (s, 3H), 3.57 (s, 3H) 1-110 Me CHF₂ CF₃ 1-111 Me Me cPr

TABLE 2 Compounds of the general formula (I) according to the invention,in which Q represents Q² and R³ represents methyl

Physical data No. X Z (¹H-NMR, DMSO-d₆, 400 MHz) 2-1 Me CF₃ 11.7 (brs,1H), 8.05 (brs, 1H), 7.95 (brs, 1H), 6.78 (brs, 1H), 3.76 (brs, 3H),3.54 (s, 3H) 2-2 Et CF₃ 11.7 (brs, 1H), 8.13 (brs, 1H), 8.04 (d, 1H),6.72 (d, 1H), 4.09 (q, 2H), 3.54 (s, 3H), 1.35 (t, 3H) 2-3 CH₂cPr CF₃2-4 C₂H₄OCH₃ CF₃ 2-5 Bn CF₃ 2-6 CH₂(3,4- CF₃ 8.08 (brd, 2H), 6.83 (d,1H), 6.79 (brs, 2H), 6.69 methylenedioxyphenyl) (d, 1H), 5.98 (s, 2H),5.33 (s, 2H), 3.62 (s, 3H) 2-7 OMe CF₃ 2-8 Me Cl 2-9 Et Cl 2-10 CH₂cPrCl 2-11 C₂H₄OCH₃ Cl 2-12 Bn Cl 2-13 OMe Cl 2-14 Me SMe 2-15 Et SMe 2-16CH₂cPr SMe 2-17 C₂H₄OCH₃ SMe 2-18 Bn SMe 2-19 OMe SMe

TABLE 3 Compounds of the general formula (I) according to the invention,in which Q represents

Physical data No. R⁴ X Z (¹H-NMR, DMSO-d₆, 400 MHz) 3-1 Me Me CF₃ 11.84(brs, 1H), 8.10 (d, 1H), 6.76 (d, 1H), 3.51 (s, 3H), 2.40 (s, 3H) 3-2 ClMe CF₃ 12.2 (brs, 1H), 8.09 (d, 1H), 6.72 (d, 1H), 3.50 (s, 3H) 3-3 MeEt CF₃ 3-4 Cl Et CF₃ 3-5 Me CH₂cPr CF₃ 3-6 Cl CH₂cPr CF₃ 3-7 Me C₂H₄OCH₃CF₃ 3-8 Cl C₂H₄OCH₃ CF₃ 3-9 Me Bn CF₃ 3-10 Cl Bn CF₃ 3-11 Me OMe CF₃3-12 Cl OMe CF₃ 3-13 Me Me Cl 3-14 Cl Me Cl 3-15 Me Et Cl 3-16 Cl Et Cl3-17 Me CH₂cPr Cl 3-18 Cl CH₂cPr Cl 3-19 Me C₂H₄OCH₃ Cl 3-20 Cl C₂H₄OCH₃Cl 3-21 Me Bn Cl 3-22 Cl Bn Cl 3-23 Me OMe Cl 3-24 Cl OMe Cl 3-25 Me MeSMe 3-26 Me Me SO₂Me 3-27 Me Me SEt 3-28 Me Me SO₂Et 3-29 Cl Me SMe 3-30Me Et SMe 3-31 Cl Et SMe 3-32 Me CH₂cPr SMe 3-33 Cl CH₂cPr SMe 3-34 MeC₂H₄OCH₃ SMe 3-35 Cl C₂H₄OCH₃ SMe 3-36 Me Bn SMe 3-37 Cl Bn SMe 3-38 MeOMe SMe 3-39 Cl OMe SMe 3-40 Me CH₂(3,4- CF₃ 11.77 (brs, 1H), 8.15 (d,1H), 6.83 (d, 1H), 6.82 methylenedioxyphenyl) (d, 1H), 6.74 (d, 1H),6.66 (dd, 1H), 5.98 (s, 2H), 5.26 (s, 2H), 2.29 (s, 3H)

TABLE 4 Compounds of the general formula (I) according to the invention,in which Q represents Q⁴

Physical data No. R⁵ X Z (¹H-NMR, DMSO-d₆, 400 MHz) 4-1 H Me CF₃ 4-2 MeMe CF₃ 8.01 (d, 1H), 6.63 (d, 1H), 3.49 (s, 3H), 2.45 (s, 3H) 4-3 Et MeCF₃ 4-4 CH₂OCH₃ Me CF₃ 4-5 H Et CF₃ 4-6 Me Et CF₃ 4-7 Et Et CF₃ 4-8CH₂OCH₃ Et CF₃ 4-9 H CH₂cPr CF₃ 4-10 Me CH₂cPr CF₃ 4-11 Et CH₂cPr CF₃4-12 CH₂OCH₃ CH₂cPr CF₃ 4-13 H C₂H₄OCH₃ CF₃ 4-14 Me C₂H₄OCH₃ CF₃ 4-15 EtC₂H₄OCH₃ CF₃ 4-16 CH₂OCH₃ C₂H₄OCH₃ CF₃ 4-17 H Bn CF₃ 4-18 Me Bn CF₃ 4-19Et Bn CF₃ 4-20 CH₂OCH₃ Bn CF₃ 4-21 H OMe CF₃ 4-22 Me OMe CF₃ 4-23 Et OMeCF₃ 4-24 CH₂OCH₃ OMe CF₃ 4-25 H Me Cl 4-26 Me Me Cl 4-27 Et Me Cl 4-28CH₂OCH₃ Me Cl 4-29 H Et Cl 4-30 Me Et Cl 4-31 Et Et Cl 4-32 CH₂OCH₃ EtCl 4-33 H CH₂cPr Cl 4-34 Me CH₂cPr Cl 4-35 Et CH₂cPr Cl 4-36 CH₂OCH₃CH₂cPr Cl 4-37 H C₂H₄OCH₃ Cl 4-38 Me C₂H₄OCH₃ Cl 4-39 Et C₂H₄OCH₃ Cl4-40 CH₂OCH₃ C₂H₄OCH₃ Cl 4-41 H Bn Cl 4-42 Me Bn Cl 4-43 Et Bn Cl 4-44CH₂OCH₃ Bn Cl 4-45 H OMe Cl 4-46 Me OMe Cl 4-47 Et OMe Cl 4-48 CH₂OCH₃OMe Cl 4-49 H Me SMe 4-50 Me Me SMe 4-51 Et Me SMe 4-52 CH₂OCH₃ Me SMe4-53 H Et SMe 4-54 Me Et SMe 4-55 Et Et SMe 4-56 CH₂OCH₃ Et SMe 4-57 HCH₂cPr SMe 4-58 Me CH₂cPr SMe 4-59 Et CH₂cPr SMe 4-60 CH₂OCH₃ CH₂cPr SMe4-61 H C₂H₄OCH₃ SMe 4-62 Me C₂H₄OCH₃ SMe 4-63 Et C₂H₄OCH₃ SMe 4-64CH₂OCH₃ C₂H₄OCH₃ SMe 4-65 H Bn SMe 4-66 Me Bn SMe 4-67 Et Bn SMe 4-68CH₂OCH₃ Bn SMe 4-69 H OMe SMe 4-70 Me OMe SMe 4-71 Et OMe SMe 4-72CH₂OCH₃ OMe SMe 4-73 Me CH₂(3,4- CF₃ 8.08 (d, 1H), 6.82 (d, 1H), 6.75(d, 1H), 6.74 methylenedioxyphenyl) (d, 1H), 6.66 (dd, 1H), 5.97 (s,2H), 5.29 (s, 2H), 2.47 (s, 3H)

TABLE 5 Compounds of the general formula (I) according to the invention,in which Q represents Q¹

Physical data No. R³ X Z F G W (¹H-NMR, DMSO-d₆, 400 MHz) 5-1 Me Me CHCH CH CH 12.05 (brs, 1H), 8.31 (dd, 1H), 7.83- 7.80 (m, 2H), 7.69-7.65(m, 1H), 7.29 (s, 1H), 4.02 (s, 3H), 3.57 (s, 3H) 5-2 Me Me CH CF CH CH5-3 Me Me N CH CH CH 12.15 (brs, 1H), 8.91 (dd, 1H), 8.27 (dd, 1H), 7.80(dd, 1H), 7.26 (s, 1H), 4.03 (s, 3H), 3.59 (s, 3H) 5-4 Me Me N CH CMe CH12.10 (brs, 1H), 8.76 (d, 1H), 8.03 (s, 1H), 7.29 (s, 1H), 4.03 (s, 3H),3.57 (s, 3H), 2.51 (s, 3H) 5-5 Me Me CH N CH CH 12.15 (brs, 1H), 9.22(dd, 1H), 8.80 (d, 1H), 8.10 (ddd, 1H), 7.41 (s, 1H), 4.03 (s, 3H), 3.59(s, 3H) 5-6 Me Me CH CH N CH 12.25 (brs, 1H), 9.48 (s, 1H), 8.84 (d,1H), 7.83 (d, 1H), 7.28 (s, 1H), 4.03 (s, 3H), 3.58 (s, 3H) 5-7 Me Me CHCH CH N 5-8 Me Me CH CMe CH N 12.13 (brs, 1H), 8.90 (d, 1H), 8.42 (m,1H), 7.17 (s, 1H), 4.02 (s, 3H), 3.57 (s, 3H), 2.51 (s, 3H) 5-9 Me Me NCH CH N 9.07 (d, 1H), 8.95 (d, 1H), 7.32 (s, 1H), 4.04 (s, 3H), 3.60 (s,3H)

TABLE 6 Compounds of the general formula (IV) in which R⁶ represents R⁷,and also compounds of the general formula (III) in which R⁶ representshydrogen and W represents hydrogen

Physical data No. R⁶ X Z (¹H-NMR, CDCl₃, 400 MHz) 6-1 Me Me H 7.48 (dd,1H), 6.7 (dd, 1H), 6.65 (dd, 1H), 3.87 (s, 3H), 3.51 (s, 3H) 6-2 H Me H7.45 (dd, 1H), 6.73 (dd, 1H), 6.60 (dd, 1H), 3.39 (s, 3H) 6-3 Me Me CF₃7.74 (d, 1H), 6.76 (d, 1H), 3.97 (s, 3H), 3.72 (s, 3H) 6-4 H Me CF₃ 7.78(d, 1H), 6.95 (d, 1H), 3.78 (s, 3H) 6-5 Et Et CF₃ DMSO-d₆: 7.73 (d, 1H),6.67 (d, 1H), 4.43 (q, 2H), 4.27 (q, 2H), 1.42 (t, 3H), 1.39 (t, 3H) 6-6H Et CF₃ DMSO-d₆: 7.75 (d, 1H), 6.88 (d, 1H), 4.36 (q, 2H), 1.40 (t, 3H)6-7 Et CH₂cPr CF₃ 7.73 (d, 1H), 6.67 (d, 1H), 4.43 (q, 2H), 4.27 (d,2H), 1.42 (t, 3H, 1.21 (m, 1H), 0.51 (m, 2H), 0.41 (m, 2H) 6-8 H CH₂cPrCF₃ 7.79 (d, 1H), 6.91 (d, 1H), 4.37 (d, 2H), 1.27 (m, 1H), 0.55-0.43(m, 4H) 6-9 Et allyl CF₃ 7.74 (d, 1H), 6.70 (d, 1H), 5.89 (m, 1H), 5.23(m, 1H), 5.17 (m, 1H), 5.01 (m, 2H), 4.37 (q, 2H), 1.39 (t, 3H) 6-10 Hallyl CF₃ 7.79 (d, 1H), 6.92 (d, 1H), 5.94 (m, 1H), 5.26-5.17 (m, 2H),5.08 (m, 2H) 6-11 Et propargyl CF₃ 7.74 (d, 1H), 6.81 (d, 1H), 5.27 (d,2H), 4.45 (q, 2H), 2.28 (t, 1H), 1.43 (t, 3H) 6-12 H propargyl CF₃ 7.80(d, 1H), 6.91 (d, 1H), 5.30 (d, 2H), 2.36 (t, 1H) 6-13 Me C₂H₄OCH₃ CF₃7.74 (d, 1H), 6.64 (d, 1H), 4.73 (t, 2H), 3.93 (s, 3H), 3.56 (t, 2H),3.25 (s, 3H) 6-14 H C₂H₄OCH₃ CF₃ 7.81 (d, 1H), 6.75 (d, 1H), 4.52 (t,2H), 3.86 (t, 2H), 3.44 (s, 3H) 6-15 Me Bn CF₃ 7.75 (d, 1H), 7.32-7.16(m, 5H), 6.67 (d, 1H), 5.66 (s, 2H), 3.77 (s, 3H) 6-16 H Bn CF₃ 7.77 (d,1H), 7.32-7.19 (m, 5H), 6.89 (d, 1H), 5.72 (s, 2H) 6-17 Et OMe CF₃ 7.72(d, 1H), 6.49 (d, 1H), 4.45 (q, 2H), 4.22 (s, 3H), 1.42 (t, 3H) 6-18 HOMe CF₃ DMSO-d₆: 8.01 (d, 1H), 6.63 (d, 1H), 4.07 (s, 3H) 6-19 Me Me Cl7.53 (d, 1H), 6.79 (d, 1H), 3.93 (s, 3H), 3.78 (s, 3H) 6-20 H Me ClDMSO-d₆: 7.80 (d, 1H), 6.78 (d, 1H), 3.62 (s, 3H) 6-21 Me OH Cl DMSO-d₆:7.79 (d, 1H), 6.59 (d, 1H), 3.87 (s, 3H) 6-22 Me OMe Cl 7.52 (d, 1H),6.55 (d, 1H), 4.22 (s, 3H), 3.96 (s, 3H) 6-23 H OMe Cl 7.54 (d, 1H),6.60 (d, 1H), 4.20 (s, 3H) 6-24 Me Me Br 7.75 (d, 1H), 6.70 (d, 1H),3.93 (s, 3H), 3.78 (s, 3H) 6-25 H Me Br DMSO-d₆: 7.88 (d, 1H), 6.69 (d,1H), 3.62 (s, 3H) 6-26 Me Me SMe DMSO-d₆: 7.17 (d, 1H), 6.96 (d, 1H),3.85 (s, 3H), 3.61 (s, 3H), 2.35 (s, 3H) 6-27 H Me SMe DMSO-d₆: 7.15 (d,1H), 6.94 (d, 1H), 3.62 (s, 3H), 2.35 (s, 3H) 6-28 Me Me SEt DMSO-d₆:7.23 (d, 1H), 6.93 (d, 1H), 3.84 (s, 3H), 3.60 (s, 3H), 2.88 (q, 2H),1.27 (t, 3H) 6-29 H Me SEt DMSO-d₆: 7.22 (d, 1H), 6.92 (d, 1H), 3.61 (s,3H), 2.87 (q, 2H), 1.27 (t, 3H)

TABLE 7 Compounds of the general formula (IV) in which R⁶ represents R⁷,and also compounds of the general formula (III) in which R⁶ representshydrogen

Physical data No. R⁶ X Z F G W (¹H-NMR, CDCl₃, 400 MHz) 7-1 Me Me CH CHCH CH 8.45 (m, 1H), 7.67 (m, 1H), 7.62- 7.58 (m, 2H), 7.26 (d, 1H), 3.96(s, 3H), 3.77 (s, 3H) 7-2 H Me CH CH CH CH DMSO-d₆: 8.32 (m, 1H), 7.71-7.69 (m, 2H), 7.59 (m, 1H), 7.29 (s, 1H), 3.72 (s, 3H) 7-3 Me Me N CH CHCH DMSO-d₆: 8.90 (dd, 1H), 8.30 (dd, 1H), 7.77 (dd, 1H), 7.34 (s, 1H),3.92 (s, 3H), 3.63 (s, 3H) 7-4 H Me N CH CH CH DMSO-d₆: 8.88 (dd, 1H),8.27 (dd, 1H), 7.75 (dd, 1H), 7.30 (s, 1H), 3.64 (s, 3H) 7-5 Me Me N CHCMe CH DMSO-d₆: 8.75 (m, 1H), 8.06 (m, 1H), 7.24 (s, 1H), 3.91 (s, 3H),3.61 (s, 3H), 2.46 (s, 3H) 7-6 H Me N CH CMe CH DMSO-d₆: 8.78 (d, 1H),8.17 (s, 1H), 7.26 (s, 1H), 3.64 (s, 3H), 2.48 (s, 3H) 7-7 Me Me CH N CHCH DMSO-d₆: 9.23 (d, 1H), 8.78 (d, 1H), 8.06 (ddd, 1H), 7.48 (d, 1H),3.93 (s, 3H), 3.63 (s, 3H) 7-8 H Me CH N CH CH DMSO-d₆: 9.22 (d, 1H),8.78 (d, 1H), 8.05 (ddd, 1H), 7.45 (d, 1H), 3.65 (s, 3H) 7-9 Me Me CH CHN CH DMSO-d₆: 9.40 (t, 1H), 8.82 (d, 1H), 7.76 (dd, 1H), 7.29 (d, 1H),3.93 (s, 3H), 3.60 (s, 3H) 7-10 H Me CH CH N CH DMSO-d₆: 9.39 (s, 1H),8.80 (d, 1H), 7.74 (dd, 1H), 7.24 (d, 1H), 3.61 (s, 3H) 7-11 Me Me CHCMe CH N DMSO-d₆: 8.88 (dd, 1H), 8.39 (m, 1H), 7.24 (d, 1H), 3.92 (s,3H), 3.61 (s, 3H), 2.48 (s, 3H) 7-12 H Me CH CMe CH N DMSO-d₆: 8.86 (dd,1H), 8.38 (m, 1H), 7.20 (d, 1H), 3.63 (s, 3H), 2.45 (d, 3H) 7-13 Me Me NCH CH N DMSO-d₆: 9.05 (d, 1H), 8.94 (d, 1H), 7.24 (d, 1H), 3.94 (s, 3H),3.63 (s, 3H) 7-14 H Me N CH CH N DMSO-d₆: 9.03 (d, 1H), 8.92 (d, 1H),7.18 (d, 1H), 3.65 (s, 3H)

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and/or salts thereof and 90 parts by    weight of talc as inert substance and comminuting the mixture in a    hammer mill.-   b) A readily water-dispersible, wettable powder is obtained by    mixing 25 parts by weight of a compound of the formula (I) and/or    salts thereof, 64 parts by weight of kaolin-containing quartz as an    inert substance, 10 parts by weight of potassium lignosulfonate and    1 part by weight of sodium oleoylmethyltaurate as a wetting agent    and dispersant, and grinding the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277° C.), and grinding the    mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as a solvent and 10 parts by weight of    ethoxylated nonylphenol as an emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium laurylsulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill and granulating the        powder in a fluidized bed by spraying on water as a granulating        liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleoylmethyltaurate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water    -   in a colloid mill, then grinding the mixture in a bead mill and        atomizing and drying the resulting suspension in a spray tower        by means of a one-phase nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action Against WeedPlants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in wood-fiber pots in sandy loam and covered with soil. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then applied asaqueous suspension or emulsion at a water application rate of 600 to 800l/ha (converted) with the addition of 0.2% of wetting agent to thesurface of the covering soil. After the treatment, the pots are placedin a greenhouse and kept under good growth conditions for the testplants. The damage to the test plants is assessed visually after a testperiod of 3 weeks by comparison with untreated controls (herbicidalactivity in percent (%): 100% action=the plants have died, 0%action=like control plants). Here, for example, the compounds Nos. 1-03,1-19, 3-01, 3-02, 1-31, 1-23, 1-04, 1-24 and 1-11, at an applicationrate of 320 g/ha, each show an activity of at least 80% againstEchinochloa crus galli, Setaria viridis, Abutilon theophrasti,Amaranthus retroflexus and Veronica persica.

2. Post-Emergence Herbicidal Action Against Weed Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then sprayed asaqueous suspension or emulsion at a water application rate of 600 to 800l/ha (converted) with the addition of 0.2% of wetting agent onto thegreen parts of the plants. After the test plants have been left to standin the greenhouse under optimal growth conditions for about 3 weeks, theaction of the formulations is assessed visually in comparison tountreated controls (herbicidal action in percent (%): 100% action=theplants have died, 0% action=like control plants). Here, for example, thecompounds Nos. 1-03, 1-19, 3-01, 3-02, 1-31, 1-23, 1-04, 1-24 and 1-11,at an application rate of 80 g/ha, each show an activity of at least 80%against Echinochloa crus galli, Amaranthus retroflexus, Matricariainodora, Stellaria media, Viola tricolor and Veronica persica.

1. A 6-pyridon-2-carbamoylazole of the formula (I) or a salt thereof

in which Q represents a radical Q¹, Q², Q³ or Q⁴,

R³ represents (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, wherethese radicals are each substituted by s radicals from the groupconsisting of halogen, cyano, hydroxy, nitro, SiR¹⁰ ₃, PO(OR¹⁰)₂,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, COR^(3a),COOR^(3a), OCOR^(3a), NR^(3a)COR^(3a), NR^(3a)SO₂R^(3b),(C₃-C₆)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the 4last-mentioned radicals are each substituted by p radicals from thegroup consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano andhalogen, and where heterocyclyl carries n oxo groups, or R³ representsphenyl which is substituted by p radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R^(3a) representshydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R^(3b)represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁴represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino,methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl,trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or representsheteroaryl, heterocyclyl or phenyl, each of which is substituted by pradicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen, R⁵ represents hydrogen, (C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, CH₂R^(5a), (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR⁶, NHR⁶, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino,methylsulfenyl, methylsulfinyl, methylsulfonyl or represents heteroaryl,heterocyclyl, benzyl or phenyl, each of which is substituted by pradicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R^(5a) represents acetoxy, acetamido,N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido,methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl,piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl,aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,(C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, or represents heteroaryl orheterocyclyl, each of which is substituted by p radicals from the groupconsisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, Xrepresents (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,OCOOR⁶, OC(O)N(R⁶)₂, OR⁶, OCOR⁶, OSO₂R⁷, (C₁-C₆)-alkyl-S(O)_(n)R⁷,(C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR⁶, (C₁-C₆)-alkyl-OSO₂R⁷,(C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶, (C₁-C₆)-alkyl-CON(R⁶)₂,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR⁶SO₂R⁷, CH₂P(O)(OR¹⁰)₂, (C₁-C₆)-alkyl-aryl,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, where the threelast-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, cyano, nitro, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries n oxo groups, Zrepresents hydrogen, halogen, cyano, thiocyanato, nitro, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR⁶, COOR⁶, OR⁶, OCOOR⁶, NR⁶COOR⁶, C(O)N(R⁶)₂, NR⁶C(O)N(R⁶)₂,OC(O)N(R⁶)₂, C(O)NR⁶OR⁶, OSO₂R⁷, S(O)_(n)R⁷, SO₂OR⁶, SO₂N(R⁶)₂,NR⁶SO₂R⁷, NR⁶COR⁶, (C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R⁷, (C₁-C₆)-alkyl-CO₂R⁶,(C₁-C₆)-alkyl-SO₂OR⁶, (C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂,(C₁-C₆)-alkyl-NR⁶COR⁶, (C₁-C₆)-alkyl-NR¹SO₂R⁷, N(R⁶)₂, P(O)(OR¹⁰)₂,heteroaryl, heterocyclyl or phenyl, where the three last-mentionedradicals are each substituted by s radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy orhalo-(C₁-C₆)-alkoxy, and where heterocyclyl carries n oxo groups, Wrepresents hydrogen, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,S(O)_(n)R¹⁰, or Z and W together with the carbon atoms to which they areattached form a five- or six-membered aromatic ring system in which pcarbon atoms are replaced by heteroatoms from the group consisting of N,O and S, and which is substituted by q radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, R⁶ representshydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycl,(C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR⁸-heteroaryl,(C₁-C₆)-alkyl-NR⁸-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO2R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R⁷ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO₂R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R⁸ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl, R⁹ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl orphenyl, R¹⁰ represents (C₁-C₄)-alkyl, n represents 0, 1 or 2, prepresents 0, 1, 2 or 3, q represents 0, 1, 2, 3 or 4, s represents 0,1, 2, 3, 4 or
 5. 2. The 6-pyridone-2-carbamoylazole or salt as claimedin claim 1 in which Q represents a radical Q¹, Q², Q³ or Q⁴,

R³ represents (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, wherethese radicals are each substituted by s radicals from the groupconsisting of halogen, cyano, nitro, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl or phenyl, where the 4 last-mentioned radicals are eachsubstituted by p radicals from the group consisting of methyl, ethyl,methoxy, trifluoromethyl, cyano and halogen, and where heterocyclylcarries n oxo groups, or R³ represents phenyl which is in each casesubstituted by p radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R⁴ represents (C₁-C₆)-alkyl,(C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,methylsulfonyl, (C₁-C₄)-alkylcarbonylamino, benzoylamino,methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl,piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino,aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,methoxymethyl, 1,2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophenyl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl,benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or phenylwhich is in each case substituted by p radicals from the groupconsisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, R⁵represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl, benzyl,pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine,dimethylamino, or phenyl substituted by p radicals from the groupconsisting of methyl, methoxy, trifluoromethyl and halogen, X represents(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,OCOOR⁶, OC(O)N(R⁶)₂, OR⁶, OCOR⁶, OSO₂R⁷, (C₁-C₆)-alkyl-S(O)_(n)R⁷,(C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR⁶, (C₁-C₆)-alkyl-OSO₂R⁷,(C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶, (C₁-C₆)-alkyl-CON(R⁶)₂,(C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶, (C₁-C₆)-alkyl-NR⁶SO₂R⁷,CH₂P(O)(OR¹⁰)₂, (C₁-C₆)-alkyl-aryl, (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkyl-heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of halogen,cyano, nitro, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries noxo groups, Z represents hydrogen, halogen, cyano, thiocyanato, nitro,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR⁶, COOR⁶, OCOOR⁶, NR⁶COOR⁶, C(O)N(R⁶)₂, NR⁶C(O)N(R⁶)₂, OC(O)N(R⁶)₂,C(O)NR⁶OR⁶, OSO₂R⁷, S(O)_(n)R⁷, SO₂OR⁶, SO₂N(R⁶)₂, NR⁶SO₂R⁷, NR⁶COR⁶,(C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R⁷, (C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶,(C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR¹SO₂R⁷, N(R⁶)₂, P(O)(OR¹⁰)₂, heteroaryl, heterocyclyl orphenyl, where the last three radicals are in each case substituted by sradicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups, W represents hydrogen, halogen,methyl, trifluoromethyl, S(O)_(n)Me, or Z and W together with the carbonatoms to which they are attached form a five- or six-membered aromaticring system in which p carbon atoms are replaced by heteroatoms from thegroup consisting of N, O and S, and which is substituted by q radicalsfrom the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, R⁶represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycl,(C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR⁸-heteroaryl,(C₁-C₆)-alkyl-NR⁸-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO2R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R⁷ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸, OCOR⁸, SCOR⁹,NR⁸COR⁸, NR⁸SO₂R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R⁸ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl, R⁹ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl orphenyl, R¹⁰ represents (C₁-C₄)-alkyl, n represents 0, 1 or 2, prepresents 0, 1, 2 or 3, q represents 0, 1, 2, 3 or 4, s represents 0,1, 2, 3, 4 or
 5. 3. The 6-pyridone-2-carbamoylazole or salt as claimedin claim 1 in which Q represents a radical Q¹, Q², Q³ or Q⁴,

R³ represents (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or (C₂-C₈)-alkynyl, each ofwhich is substituted by s radicals from the group consisting of halogen,cyano, nitro, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy, R⁴ represents (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano, nitro,methylsulfenyl, methylsulfinyl, methylsulfonyl,(C₁-C₄)-alkylcarbonylamino, benzoylamino, methoxycarbonyl,ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,1,2,4-triazol-1H, 1-pyrazol-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 1,2,4-oxadiazol-3-yl, benzoxazol-2-yl,1-ethylbenzimidazol-2-yl, piperidin-1-yl, or represents phenyl which isin each case substituted by s radicals from the group consisting ofmethyl, ethyl, methoxy, trifluoromethyl and halogen, R⁵ representshydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazin-2-yl,furan-2-yl, tetrahydrofuran-2-yl, morpholine, dimethylamino, or phenylsubstituted by p radicals from the group consisting of methyl, methoxy,trifluoromethyl and halogen, X represents (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, OR⁶, S(O)_(n)R⁷,(C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-CON(R⁶)₂,(C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶, (C₁-C₆)-alkyl-NR⁶SO₂R⁷,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkylheterocyclyl, where the twolast-mentioned radicals are in each case substituted by s radicals fromthe group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups, Z represents hydrogen, halogen,cyano, thiocyanato, nitro, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR⁶, COOR⁶, OCOOR⁶, NR⁶COOR⁶, C(O)N(R⁶)₂, NR⁶C(O)N(R⁶)₂, OC(O)N(R⁶)₂,C(O)NR⁶OR⁶, OSO₂R⁷, S(O)_(n)R⁷, SO₂OR⁶, SO₂N(R⁶)₂, NR⁶SO₂R⁷, NR⁶COR⁶,(C₁-C₆)-alkyl-S(O)_(n)R⁷, (C₁-C₆)-alkyl-OR⁶, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R⁷, (C₁-C₆)-alkyl-CO₂R⁶, (C₁-C₆)-alkyl-SO₂OR⁶,(C₁-C₆)-alkyl-CON(R⁶)₂, (C₁-C₆)-alkyl-SO₂N(R⁶)₂, (C₁-C₆)-alkyl-NR⁶COR⁶,(C₁-C₆)-alkyl-NR¹SO₂R⁷, N(R⁶)₂, P(O)(OR¹⁰)₂, heteroaryl, heterocyclyl orphenyl, where the 3 last-mentioned radicals are in each case substitutedby s radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups, W represents hydrogen,chlorine, methyl or trifluoromethyl, or Z and W together with the carbonatoms to which they are attached form a five- or six-membered aromaticring system in which p carbon atoms are replaced by heteroatoms from thegroup consisting of N, O and S, and which is substituted by q radicalsfrom the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₄)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-methyl,(C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, R⁶ represents hydrogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycl,(C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR⁸-heteroaryl,(C₁-C₆)-alkyl-NR⁸-heterocyclyl, where the 21 last-mentioned radicals arein each case substituted by s radicals from the group consisting ofcyano, halogen, nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸,COR⁸, OCOR⁸, SCOR⁹, NR⁸COR⁸, NR⁸SO2R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R⁷ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals areeach substituted by s radicals from the group consisting of cyano,halogen, nitro, thiocyanato, OR⁸, S(O)_(n)R⁹, N(R⁸)₂, NR⁸OR⁸, COR⁸,OCOR⁸, SCOR⁹, NR⁸COR⁸, NR⁸SO₂R⁹, CO₂R⁸, COSR⁹, CON(R⁸)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R⁸ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl, R⁹ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl orphenyl, R¹⁰ represents (C₁-C₄)-alkyl, n represents 0, 1 or 2, prepresents 0, 1, 2 or 3, q represents 0, 1, 2, 3 or 4, s represents 0,1, 2, 3, 4 or
 5. 4. A herbicidal composition which comprises aherbicidally effective amount of at least one compound as claimed inclaim
 1. 5. The herbicidal composition as claimed in claim 4 in amixture with one or more formulation auxiliaries.
 6. The herbicidalcomposition as claimed in claim 4, comprising at least one furtherpesticidally active substance selected from the group consisting ofinsecticides, acaricides, herbicides, fungicides, safeners and growthregulators.
 7. The herbicidal composition as claimed in claim 6,comprising a safener.
 8. The herbicidal composition as claimed in claim7, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl orisoxadifen-ethyl.
 9. The herbicidal composition as claimed in claim 6,comprising a further herbicide.
 10. A method for controlling unwantedplants, comprising applying an effective amount of at least one compoundas claimed in claim 1 to one or more plants or to a site of unwantedplants.
 11. A compound as claimed in claim 1 capable of being used forcontrolling unwanted plants.
 12. A compound as claimed in claim 11,wherein the compound of formula (I) is used for controlling one or moreunwanted plants in one or more crops of one or more useful plants. 13.The compound as claimed in claim 12, wherein the useful plants aretransgenic useful plants.